Carboxylic Acids: Properties and Synthesis Chapter 18 Carboxylic Acids: Properties and Synthesis WWU- Chemistry

Assignments In-text problems: End-of-chapter problems: 18-1 and 18-2 18-4 (IUPAC only!!) 18-6 to 18-10 18-14 to 18-20 End-of-chapter problems: 1 3 to 9 11 to 16 WWU- Chemistry

Sect. 18.1: IUPAC Nomenclature -oic acid IUPAC ending -carboxylic acid IUPAC ending for ring compounds WWU- Chemistry

3-Methylbutanoic acid WWU- Chemistry

2-Chloropentanoic acid WWU- Chemistry

4-methoxy-3,5-hexadienoic acid WWU- Chemistry

Cyclohexanecarboxylic acid WWU- Chemistry

3-methylcyclohexanecarboxylic acid WWU- Chemistry

or Benzenecarboxylic acid Benzoic acid or Benzenecarboxylic acid WWU- Chemistry

Numbering system WWU- Chemistry

or 2-chlorobenzenecarboxylic acid 2-chlorobenzoic acid or 2-chlorobenzenecarboxylic acid WWU- Chemistry

Common names for benzoic acids WWU- Chemistry

ortho-chlorobenzoic acid Common names! ortho-chlorobenzoic acid o-chlorobenzoic acid WWU- Chemistry

IUPAC only 3-chloro-2-nitrobenzoic acid or 3-chloro-2-nitrobenzenecarboxylic acid WWU- Chemistry

IUPAC only 3-(3-nitrophenyl)propanoic acid WWU- Chemistry

Common Names WWU- Chemistry

Some more common names butyric acid and isobutyric acid valeric acid and isovaleric acid Fatty acids: myristic, palmitic and stearic acids WWU- Chemistry

2-Methylpropanoic acid Isobutyric acid WWU- Chemistry

Fatty acids WWU- Chemistry

Sect. 18.2: carboxylate salts endings: oate combine with sodium, potassium etc. Example: sodium butanoate (IUPAC) or sodium butyrate (common) WWU- Chemistry

Carboxylate Ion Formation WWU- Chemistry

Sect. 18.3: hydrogen bonding Carboxylic acids are very high boiling! Low MW acids are water soluble and High MW acids are water insoluble! WWU- Chemistry

Sections 18.4, 18.5, 18.6 Much of this material is review! Key table: Table 18-18 on page 62!! Skip Section 18.7. WWU- Chemistry

Resonance Effects Effect Acid Base Examples Electron weaken strengthen withdrawing by resonance (-R) strengthen weaken releasing by Resonance (+R) Electron weaken strengthen WWU- Chemistry

Electron-withdrawing effects involving resonance (-R) These substituents strengthen acids and weaken bases on the benzene ring WWU- Chemistry

Substituents with Electron-Withdrawing Resonance Effects WWU- Chemistry

Electron-withdrawing Effects: strengthen acids weaken bases WWU- Chemistry

A substituted benzoic acid WWU- Chemistry

Electron releasing effect by resonance (+R) These substituents weaken acids and strengthen bases on the benzene ring WWU- Chemistry

Substituents with Electron-Releasing Resonance Effects WWU- Chemistry

Electron-releasing Effects: - weaken acids - strengthen bases WWU- Chemistry

Substituted benzoic acid WWU- Chemistry

Benzoic Acid: pKa = 4.19 WWU- Chemistry

Inductive Effect Effect Acid Base Examples Electron withdrawing by strengthen weaken electron releasing by inductive effect (+I) weaken strengthen WWU- Chemistry

Electron withdrawing by inductive effects (-I) These substituents strengthen acids and weaken bases WWU- Chemistry

Substituents with Electron-Withdrawing Inductive Effects on substituted acetic acids WWU- Chemistry

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Resonance and weak inductive and resonance Inductive, only Resonance and weak inductive Benzoic Acid: pKa = 4.19 WWU- Chemistry

Another substituted benzoic acid 4-chlorobenzoic acid is weird!! Resonance effect will decrease acidity, but inductive effect wins out. WWU- Chemistry

Electron releasing effect by inductive effect (+I) These substituents weaken acids and strengthen bases WWU- Chemistry

Substituents with Electron-Releasing Inductive Effects WWU- Chemistry

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Benzoic Acid: pKa = 4.19 WWU- Chemistry

Sect. 18.8: Carbonation of Grignard Reagents WWU- Chemistry

Sect. 18.9: Formation of Nitriles WWU- Chemistry

Hydrolysis of Nitriles WWU- Chemistry

Sect. 18.10: Oxidation of Primary Alcohols WWU- Chemistry

Oxidation of Side Chains WWU- Chemistry

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